$262+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Cayman Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Jose to Cayman Islands
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Best
Last-minute
One-way
Cheapest flights from San Jose to Cayman IslandsExplore the most affordable flight options available from San Jose to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from San Jose to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
2 stops10h 53m
Wed 11/253:40 pm -
2 stops22h 04m
Deal found 10/4![American Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:10 pm -
2 stops21h 20m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 9/30![United Airlines logo]()
$702
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:16 pm -
2 stops17h 09m
Mon 10/262:10 pm -
2 stops22h 54m
Deal found 10/5![American Airlines logo]()
$703
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:00 am -
2 stops10h 53m
Fri 1/84:07 pm -
2 stops22h 06m
Deal found 9/30![American Airlines logo]()
$753
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2910:30 pm -
1 stop11h 42m
Fri 1/82:05 pm -
1 stop9h 53m
Deal found 9/30![Delta logo]()
$850
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:43 pm -
2 stops19h 42m
Wed 11/251:50 pm -
1 stop11h 22m
Deal found 10/4![Delta logo]()
$855
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:45 pm -
1 stop10h 55m
Sun 10/2512:55 pm -
1 stop10h 30m
Deal found 10/5![Delta logo]()
$867
Best flights from San Jose to Cayman IslandsDiscover carefully curated flight deals from San Jose to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from San Jose to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/152:24 pm -
2 stops22h 36m
Sat 1/235:10 pm -
2 stops21h 59m
Deal found 10/4![United Airlines logo]()
$634
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:00 am -
2 stops10h 53m
Fri 1/84:07 pm -
2 stops22h 06m
Deal found 10/1![American Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:10 pm -
2 stops21h 20m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/1![United Airlines logo]()
$702
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Fri 1/153:12 pm -
1 stop20h 18m
Sat 1/233:30 pm -
1 stop9h 42m
Deal found 10/4![American Airlines logo]()
$794
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/292:26 pm -
2 stops23h 09m
Fri 1/82:55 pm -
2 stops25h 26m
Deal found 10/4![United Airlines logo]()
$764
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:41 pm -
2 stops18h 19m
Mon 10/122:10 pm -
2 stops22h 54m
Deal found 10/2![American Airlines logo]()
$1,004
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:45 pm -
1 stop10h 55m
Sun 10/2512:55 pm -
1 stop10h 30m
Deal found 10/5![Delta logo]()
$867
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:16 pm -
2 stops17h 09m
Mon 10/262:10 pm -
2 stops22h 54m
Deal found 10/5![American Airlines logo]()
$703
This Mytrip deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:59 pm -
3 stops19h 46m
Mon 10/262:35 pm -
3 stops27h 16m
Deal found 10/5![WestJet logo]()
$1,447
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:10 pm -
2 stops21h 20m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 9/30![United Airlines logo]()
$702
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
2 stops10h 53m
Wed 11/253:40 pm -
2 stops22h 04m
Deal found 10/4![American Airlines logo]()
$639
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:43 pm -
2 stops19h 42m
Wed 11/251:50 pm -
1 stop11h 22m
Deal found 10/4![Delta logo]()
$855
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:45 am -
2 stops28h 45m
Thu 11/265:45 pm -
2 stops30h 23m
Deal found 10/5![United Airlines logo]()
$1,335
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:50 pm -
2 stops15h 45m
Sat 11/282:20 pm -
2 stops19h 55m
Deal found 10/3![Southwest logo]()
$1,454
One-way flights from San Jose to Cayman IslandsSearch for one-way flight options from San Jose to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from San Jose to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 pm -
2 stops16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:50 pm -
2 stops15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:38 am -
3 stops25h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![WestJet logo]()
$458
This Mytrip deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
3 stops27h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$471
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/275:00 pm -
2 stops16h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:40 pm -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Delta logo]()
$872
Find flight deals from San Jose to Cayman Islands
Keep the following information in mind while searching for San Jose to Cayman Islands flight deals. Data was last updated October 5, 2026.
Round-trip from | $634 (United Airlines) |
|---|---|
One-way from | $262 (Southwest) |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 5, 2026.
Use the filters below to find and compare flights from San Jose to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 11/18
5:30 pm-12:35 pm
2 stops16h 05m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$262
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 11/19
5:50 pm-12:35 pm
2 stops15h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$321
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 2/27
5:00 pm-12:40 pm
2 stops16h 40m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$528
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 1/15
2:24 pm-4:00 pm
2 stops22h 36m
George Town Owen Roberts Intl
Sat 1/23
5:10 pm-12:09 pm
2 stops21h 59m
$634
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 11/2
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Thu 11/5
5:45 pm-10:59 pm
2 stops32h 14m
$702
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
6:00 am-7:53 pm
2 stops10h 53m
George Town Owen Roberts Intl
Fri 1/8
4:07 pm-11:13 am
2 stops22h 06m
$753
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
2:26 pm-4:35 pm
2 stops23h 09m
George Town Owen Roberts Intl
Fri 1/8
2:55 pm-1:21 pm
2 stops25h 26m
$764
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 1/15
3:12 pm-2:30 pm
1 stop20h 18m
George Town Owen Roberts Intl
Sat 1/23
3:30 pm-10:12 pm
1 stop9h 42m
$794
Quickest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 11/19
10:40 pm-12:25 pm
1 stop10h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$872
Sorted by cheapest first
Best time to book a flight from San Jose to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from San Jose with our price prediction graph.
SJC-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Jose to the Cayman Islands
SJC-KY0
SJC-GCM
No data available for this route at this time. Please check back soon.
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